Tariric acid di-iodid.



1 No Drawing.

7 UNITED STATES PATENT OFFICE.

ALBERT LEON ARNAUD'AND SWIGEL POSTERNAK, OF PARIS, FRANCE, ASSIGNOBS TO THE FIRM OF E. HOFFMAN-LA KOCH]? AND COMPANY, OF GRENZNACH, GERMANY.

" NAUD, a .citizen of the French Republic,

and SWIGEL Pos'rnRNAK, a subject of the Emperor of Russia, residing at Paris, France,

have invented certain new and useful Im-' provements Relating to Compounds of Ta1'iric Acid, of WlllCl'l the following is a specification.

The tariric acid combined with glycerin. .in the fruits of various kinds ofipicramnia 1 was dlscov'eredquite a long time ago by one of us as the first naturally occurring fatt acid with-av triple carbon bond. As suc it is able to add on one or two molecules of a halogen. Hitherto the addition'of iodin to unsaturated fatty acids has, however, been a difficult task. Liebermann and Sachse (Bem'chte der Deut. Chem. Gesellschaft, 24, p. 4116) only succeeded in doing so in a troublesome manner, 6. g. in the case. of stearolic and behenolic acids, when they subjected carbon disulfid solutions of these acids to light for several days in the presence of molecular quantities of iodin and some ferrous iodid, without thereby obtaining good yields. \Ve have therefore gone to work in a difl'erent way, to obtain from tariric acid the asyet entirely unknown diiodo derivative, and we have found that the addition of a molecule of iodin to this acid takes place rapidly and almost quantita tively, if the reaction be conducted in a solution of glacial acetic acid at temperatures between 50 and degrees centig'rade. We have also found that the introduction of two atoms of iodin into tariric acid can also be effected in aqueous solution in an easy manner and not quite so well in chloroform, benzene and similar solvents of fatty acids. 7 I

The details of procedure will be'explained below by the aid of two examples.

Example I: One part of weight of tariric acid C H O, v(00m tes Rendus d6 ZAcademz'e des Sciences XXII, 1000) is dis-v solved in 3 parts by weight of warm glacial acetic acid; to this solution are added slowly and with stirring 0.91 parts by weight of solid iodin. The whole is allowed to stand for an hour and the mixture, after having been decolorized with sulfurous acid by conducting the latter in gaseous shape into the solution of glacial acid until the desired effect is obtained, is poured into about 20 pure form. The

'""f Specification ojf Letters Patent. 4 Patented Jan. 24;, 1911- Application filed October is, 1909. Serial No. 528,347.

' To all avho'm 'it may concern: I Be 1tknown that we, ALBERT LnoN AR-i.

liquor, is dissolved in warm alcohol'and decomposed by a dilute mineral acid, such for example as sulfuric acid. The free di-iodoacid then crystallizes out in a chemically tariric acid -di -iodid C H O l crystallizes in the shape of fine white needles which melt at 48.5 C. and

contain 47.56 of iodin. The di-iodid is insoluble in water, easily soluble in alcohol parts of warm water. The oily deposit when heated, insoluble in cold glycerin, but

slightly soluble when heated. The chemical constitution of the compound maybe indicated-by the formula: I

Example II: One part by weight of tariric acid is dissolved in 10 parts by weight of boiling water, to which has been added caustic soda equal to 1/7 of the Weight of the acid. After cooling down, 9 parts by weight of a mixture of 100 grams of iodin, 160 grams of potassium iodid and 740 grams of water are slowly poured into the solution. From the red solution obtained the iodo fatty acid is precipitated with dilute sulfuric' acid, filtered and washed with water, after which it is finally further purified and crystallized as described in Example I. It is obvious that the caustic soda can be replaced by the equivalent quantities of caustic potash, sodium carbonate, etc., and the sulfuric acid by another mineral acid. If caustic potash is used 0.20 parts of the same, and if sodium carbonate is used 0.189 parts of the same are dissolved in 10 parts of water.

The di-iodid of tariric acid provides an extraordinarily manageable and, owing to its very intense action, valuable body for iodin therapeutics.

Whatwe claim is 1. The process for the manufacture of tariric acid di-iodid, which consists in dissolving tariric acid in a solvent and reacting upon the solution with iodin, substantially 0 1 1 0 1 crystallizing as white needles,

as described. melting at 48.5' C. and containing 47.56

2. The process for the manufacture of tariper cent. of iodin,'substantially as described. 15 ric acid di-iodid, which consists in dissolv- In testimony whereof we have hereunto 5 ing tariric acid in glacial acetic acid, treatset our hands in presence of two subscribing mg the solution with iodin, decolorizing witnesses.

with sulffurous acid the mixture thus ob- ALBERT LEON ARNAUD tained orming a precipitate by mixing with water and crystallizing the precipitate, SWIGEL POSTERNAK' 10 after congealing, by means of alcohol, sub- Witnesses:

stantially as described. GEORGE E. LIGHT,

3. As a new product, tariric acid di-iodid H. C. CoXE. 

